Tetrahedron: Asymmetry

Synthesis, olfactory evaluation and determination of the absolute configuration of the β-and γ-Iralia® isomers

A Barakat, E Brenna, C Fuganti, S Serra

Index: Barakat, Assem; Brenna, Elisabetta; Fuganti, Claudio; Serra, Stefano Tetrahedron Asymmetry, 2008 , vol. 19, # 19 p. 2316 - 2322

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Citation Number: 9

Abstract

The regioselective synthesis of the methyl-ionone isomers 6–9 is described. The enantiomers of the γ-isomers 8 and 9 are prepared by enzyme-mediated resolution of the corresponding 4-hydroxy derivatives followed by reductive elimination of the hydroxy group. The absolute configuration of the latter compound is determined by chemical correlation with the known α-isomers. Since all the isomers obtained are components of the artificial violet ...